JPS5980624A - ベンゼン誘導体の製造方法 - Google Patents
ベンゼン誘導体の製造方法Info
- Publication number
- JPS5980624A JPS5980624A JP9872983A JP9872983A JPS5980624A JP S5980624 A JPS5980624 A JP S5980624A JP 9872983 A JP9872983 A JP 9872983A JP 9872983 A JP9872983 A JP 9872983A JP S5980624 A JPS5980624 A JP S5980624A
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- toluene
- reaction
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 25
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 238000005660 chlorination reaction Methods 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- OSOLHARQJQEMBZ-UHFFFAOYSA-N 1-chloropentylbenzene Chemical compound CCCCC(Cl)C1=CC=CC=C1 OSOLHARQJQEMBZ-UHFFFAOYSA-N 0.000 claims description 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 6
- ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 3
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 238000006007 Sommelet synthesis reaction Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006487 butyl benzyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3397/82-0 | 1982-06-03 | ||
| CH3397/82A CH648276A5 (en) | 1982-06-03 | 1982-06-03 | Process for the preparation of benzene derivatives |
| CH2083/83 | 1983-04-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5980624A true JPS5980624A (ja) | 1984-05-10 |
| JPS6311340B2 JPS6311340B2 (enrdf_load_stackoverflow) | 1988-03-14 |
Family
ID=4255096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9872983A Granted JPS5980624A (ja) | 1982-06-03 | 1983-06-02 | ベンゼン誘導体の製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5980624A (enrdf_load_stackoverflow) |
| BE (1) | BE896932A (enrdf_load_stackoverflow) |
| CH (1) | CH648276A5 (enrdf_load_stackoverflow) |
-
1982
- 1982-06-03 CH CH3397/82A patent/CH648276A5/de not_active IP Right Cessation
-
1983
- 1983-06-02 BE BE0/210910A patent/BE896932A/fr not_active IP Right Cessation
- 1983-06-02 JP JP9872983A patent/JPS5980624A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH648276A5 (en) | 1985-03-15 |
| BE896932A (fr) | 1983-12-02 |
| JPS6311340B2 (enrdf_load_stackoverflow) | 1988-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Matteson | Chlorination of Methaneboronic Acid Derivatives with t-Butyl Hypochlorite | |
| JPS5946212B2 (ja) | グリオキザ−ルの製造方法 | |
| US4036899A (en) | Synthesis of prenyl chloride | |
| US2932665A (en) | Preparation of nu, nu-diethyltoluamides | |
| Westberg et al. | Thermolysis of pentacyclo [4.4. 0.0. 2, 50.3, 804, 7] dec-9-ene | |
| US4853489A (en) | Selective chlorination of para-tertiary-butytoluene | |
| JPS5980624A (ja) | ベンゼン誘導体の製造方法 | |
| He et al. | The photochemical synthesis of α, α, α-bromodifluorotoluene and α, α, α-chlorodifluorotoluene | |
| US3192275A (en) | Process for making fulvenes | |
| US2443494A (en) | Preparation of unsaturated chloronitriles | |
| Campbell et al. | Preparation and chemistry of some 1-iodo-1-phenylpropenes | |
| Nozakura | Addition of Trichlorosilane to Acetylene and to Vinyltrichlorosilane | |
| US2921942A (en) | Synthesis of carbazole | |
| US2655474A (en) | Photochemical production of olefinic hydrocarbons | |
| US1816843A (en) | Method for preparing alkali metal alcoholates | |
| US3497435A (en) | Photoisomerization of alpha,alpha'-dimethylmuconic acid | |
| CA2138943A1 (en) | Process for the oxidation of aromatic methyl groups | |
| JPH02235857A (ja) | ビス―（４―ヒドロキシフエニル）―スルフオンの製造方法 | |
| US3860614A (en) | Thermolysis of styrene oxide | |
| US3367857A (en) | Side-chain chlorination of ringsubstituted acetophenones | |
| RU2118308C1 (ru) | Способ получения 1,1,1-трихлортрифторэтана | |
| KR20030062357A (ko) | 기상 알칸의 광화학적 술포클로린화 방법 | |
| ATE265407T1 (de) | Verbessertes verfahren zur herstellung von hexabromcyclododecan | |
| US3140246A (en) | Preparation of aromatic acid halides | |
| US3102134A (en) | Preparation of menthenyl esters and ethers |